22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester (CHEM033603)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 04:17:37 UTC
Update Date2016-11-09 01:20:57 UTC
Accession NumberCHEM033603
Identification
Common Name22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester
ClassSmall Molecule
Description22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester is found in fruits. 22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester is a constituent of Physalis peruviana (Cape gooseberry).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
22R-Acetoxy-1a,3b-dihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
22R-Acetoxy-1a,3b-dihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
22R-Acetoxy-1α,3β-dihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
22R-Acetoxy-1α,3β-dihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-6-acetyl-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] esterGenerator
6-[(Acetyloxy)methyl]-3-({6-[(acetyloxy)methyl]-3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl (2Z)-5-(acetyloxy)-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoic acidGenerator
Chemical FormulaC58H90O28
Average Molecular Mass1235.318 g/mol
Monoisotopic Mass1234.562 g/mol
CAS Registry Number151194-19-3
IUPAC Name6-[(acetyloxy)methyl]-3-({6-[(acetyloxy)methyl]-3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl (2Z)-5-(acetyloxy)-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoate
Traditional Name6-[(acetyloxy)methyl]-3-({6-[(acetyloxy)methyl]-3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)-4,5-dihydroxyoxan-2-yl (2Z)-5-(acetyloxy)-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoate
SMILESCC(C(C\C(C)=C(\C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC1OC(COC(C)=O)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)OC(C)=O)C1CCC2C3CC=C4CC(CC(O)C4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O
InChI IdentifierInChI=1S/C58H90O28/c1-22(15-34(78-27(6)63)24(3)31-11-12-32-30-10-9-28-16-29(79-53-47(72)43(68)40(65)35(18-59)80-53)17-39(64)58(28,8)33(30)13-14-57(31,32)7)23(2)52(75)86-56-51(45(70)42(67)37(82-56)20-76-25(4)61)85-55-49(74)46(71)50(38(83-55)21-77-26(5)62)84-54-48(73)44(69)41(66)36(19-60)81-54/h9,24,29-51,53-56,59-60,64-74H,10-21H2,1-8H3/b23-22-
InChI KeyWROICLPHNFHHKX-FCQUAONHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Ergostane-skeleton
  • Steroidal glycoside
  • Oligosaccharide
  • Hydroxy bile acid, alcohol, or derivatives
  • Monohydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • Steroid ester
  • Diterpenoid
  • 1-hydroxysteroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Terpene glycoside
  • Tetracarboxylic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Cyclic alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Polyol
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.69 g/LALOGPS
logP-0.27ALOGPS
logP-2.5ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area432.8 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity287.66 m³·mol⁻¹ChemAxon
Polarizability128.11 ųChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9360128040-9e46095e6dd5a5138fdbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0aor-9130455353-d079b97b524fb5bb2ddcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9281554453-4a32fef3ab6ffbdf785dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0aov-9541013020-87fffabfec4ba3da12a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-9322003020-50aa2493473e42cb5a71Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9622000212-e2ba0acb1089c6040bf3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3920245100-c651f640ae9055d0bad2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i09-5970436202-e6e21cc10cd3976b3a65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-8921200000-4cf8d5f29db766640756Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1950033000-6103aba260694d0bc7cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6910001000-96c395dad4a16c5b2570Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9500000000-8ca3f17a1e52b1321867Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0040404
FooDB IDFDB020136
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID131752815
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM